237406-95-0Relevant academic research and scientific papers
Synthetic studies on 2'-substituted-4'-thiocytidine derivatives as antineoplastic agents
Yoshimura, Yuichi,Endo, Mikari,Kitano, Kenji,Yamada, Kohei,Sakata, Shinji,Miura, Shinji,Machida, Haruhiko
, p. 815 - 820 (2007/10/03)
As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.
An Alternative Synthesis of the Antineoplastic Nucleoside 4′-ThioFAC and Its Application to the Synthesis of 4′-ThioFAG and 4′-Thiocytarazid
Yoshimura, Yuichi,Endo, Mikari,Miura, Shinji,Sakata, Shinji
, p. 7912 - 7920 (2007/10/03)
Previously, we synthesized 4′-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method for the synthesis of 4′-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the 1-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a β-anomer of 4′-thioFAC. The reaction of 2,6-diaminopurine with the 1-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a β-anomer of 4′-thioFAG, a guanine congener of 4′-thioFAC, selectively. Using a similar approach, we synthesized 4′-thiocytarazid, which was not possible using the original method.
